947596-41-0Relevant academic research and scientific papers
Asymmetric Total Synthesis of Cerorubenic Acid-III
Liu, Xin,Liu, Junyang,Wu, Jianlei,Huang, Guocheng,Liang, Rong,Chung, Lung Wa,Li, Chuang-Chuang
, p. 2872 - 2877 (2019)
The first asymmetric total synthesis of the highly strained compound cerorubenic acid-III is reported. A type II intramolecular [5 + 2] cycloaddition allowed efficient and diastereoselective construction of the synthetically challenging bicyclo[4.4.1] ring system with a strained bridgehead (anti-Bredt) double bond in the final product. A unique transannular cyclization installed the vinylcyclopropane moiety with retention of the desired stereochemistry.
Expedient synthesis of bisabolenol stink bug pheromones via stereodefined cyclohex-2-enones
Shirali, Shyam,Guzman, Filadelfo,Weber, Donald C.,Khrimian, Ashot
supporting information, p. 2066 - 2068 (2017/05/04)
We recently synthesized all stereoisomers of 1,10-bisaboladien-3-ol and 10,11-epoxy-1-bisabolen-3-ol, including three stink bug pheromones, via a rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones. However, yields of trans isomers were low, and scaling reactions using expensive catalysts were cumbersome. Now we describe a new synthesis of bisabolenol stink bug pheromones via (S)- and (R)-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enones prepared by enantioselective Michael additions of methyl vinyl ketone to (S)- and (R)-citronellals and lithium hydroxide monohydrate-catalyzed stereoselective cyclizations of intermediate ketoaldehydes. Addition of methyllithium to these enones provided cis- and trans-1,10-bisaboladien-3-ols, which were separated by chromatography on silica and further converted to 10,11-epoxy-1-bisabolen-3-ols. Thus, we developed more convenient syntheses of pheromones of the rice stink bug, the harlequin bug, and brown marmorated stink bug.
Total synthesis and structural revision of biyouyanagin B
Nicolaou,Sanchini, Silvano,Wu, T. Robert,Sarlah, David
supporting information; experimental part, p. 7678 - 7682 (2010/09/05)
Figure Presented An intriguing chase of the newly reported biyouyanagin B leads to its total synthesis and structural revision from 1' to 1.
Total synthesis, revised structure, and biological evaluation of biyouyanagin A and analogues thereof
Nicolaou,Wu, T. Robert,Sarlah, David,Shaw, David M.,Rowcliffe, Eric,Burton, Dennis R.
supporting information; experimental part, p. 11114 - 11121 (2009/02/05)
Isolated from Hypericum species H. Chinese L. var. salicifolium, biyouyanagin A was assigned structure 1a or 1b on the basis of NMR spectroscopic analysis. This novel natural product exhibited significant anti-HIV properties and inhibition of lipopolysacc
